Fisetin

Names

[ CAS No. ]:
528-48-3

[ Name ]:
Fisetin

[Synonym ]:
5-Deoxyquercetin
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-
Fisetin
Viset
3,3',4',7-tetrahydroxyflavone
MFCD00006829
Fustet
Superfustel
Cotinin
Fustel
Fisidenolon 1521
5-Desoxyquercetin
3,7-Dihydroxy-2-(3,4-dihydroxyphenyl)-4H-1-benzopyran-4-one
2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one
2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one
Fietin
EINECS 208-434-4
3,7,3',4'-Tetrahydroxyflavone
Fisetholz

Biological Activity

[Description]:

Fisetin is a natural flavonol found in many fruits and vegetables with various benefits, such as antioxidant, anticancer, neuroprotection effects.

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> PPAR

Signaling Pathways >> Cell Cycle/DNA Damage >> Sirtuin

Signaling Pathways >> Epigenetics >> Sirtuin

Signaling Pathways >> Apoptosis >> TNF Receptor

Natural Products >> Flavonoids

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

[Target]

Sirtuin, PPAR, TNF-alpha[1][2]

[In Vitro]

Fisetin inhibits lipid accumulation and suppresses the expression of PPARγ in 3T3-L1 cells. Fisetin suppresses early stages of preadipocyte differentiation, and induces expression of Sirt1. Fisetin facilitates Sirt1-mediated deacetylation of PPARγ and FoxO1, and enhances the association of Sirt1 with the PPARγ promoter, leading to suppression of PPARγ transcriptional activity, thereby repressing adipogenesis[1]. Fisetin binds to tubulin and stabilizes microtubules with binding characteristics far superior than paclitaxel. Fisetin treatment of human prostate cancer cells results in robust up-regulation of microtubule associated proteins (MAP)-2 and -4. Fisetin significantly inhibits PCa cell proliferation, migration, and invasion. Nudc, a protein associated with microtubule motor dynein/dynactin complex that regulates microtubule dynamics, is inhibited with Fisetin treatment[2].

[In Vivo]

Fisetin treatment to UVB exposed mice results in decreased hyperplasia and reduces infiltration of inflammatory cells. Fisetin treatment also reduces inflammatory mediators such as COX-2, PGE2 as well as its receptors (EP1- EP4), and MPO activity. Furthermore, Fisetin reduces the level of inflammatory cytokines TNFα, IL-1β and IL-6 in UVB exposed skin. Fisetin treatment also reduces cell proliferation markers as well as DNA damage as evidenced by increased expression of p53 and p21 proteins[3].

[Cell Assay]

3T3-L1 cells are transfected with reporter vector, and expression plasmids using TransIT-LT1. After 24 h, media is replaced with viral supernatant. After 15-18 h of infection, media is replaced with DMI, 0.1 μM troglitazone and Fisetin (50 μM). Cells are lysed using cell culture lysis buffer two days after addition of differentiation stimulus. Luciferase activity is determined using an analytical luminescence luminometer[1].

[Animal admin]

Mice: The mice are divided into six groups of eight animals each. The mice in the first group are topically treated with 0.2 mL acetone and used as vehicle control. The mice in the second and third groups receive topical treatment of Fisetin 250 nmol/0.2 mL acetone/mouse and 500 nmol/0.2 mL acetone/mouse respectively on their dorsal skin and serves as agent controls. The mice in the fourth, fifth and sixth groups are exposed to UVB. The mice in the fourth group receive a topical application of 0.2 mL acetone after 15 min of UVB exposure designated as vehicle control. The mice in the fifth and sixth groups are treated with topical application of Fisetin 250 nmol/0.2 mL acetone/mouse and 500 nmol/0.2 mL acetone/mouse respectively on to their dorsal skin after 15 min of UVB exposure[3].

[References]

[1]. Kim SC, et al. Fisetin induces Sirt1 expression while inhibiting early adipogenesis in 3T3-L1 cells. Biochem Biophys Res Commun. 2015 Nov 27;467(4):638-44.

[2]. Mukhtar E, et al. Dietary flavonoid fisetin binds to β-tubulin and disrupts microtubule dynamics in prostate cancer cells. Cancer Lett. 2015 Oct 28;367(2):173-83.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
599.4±50.0 °C at 760 mmHg

[ Melting Point ]:
330ºC

[ Molecular Formula ]:
C₁₅H₁₀O₆

[ Molecular Weight ]:
286.236

[ Flash Point ]:
233.0±23.6 °C

[ Exact Mass ]:
286.047729

[ PSA ]:
111.13000

[ LogP ]:
2.52

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.785

[ Storage condition ]:
−20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LK9250000

CHEMICAL NAME :: Flavone, 3,3',4',7-tetrahydroxy-

CAS REGISTRY NUMBER :: 528-48-3

BEILSTEIN REFERENCE NO. :: 0292829

LAST UPDATED :: 199701

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C15-H10-O6

MOLECULAR WEIGHT :: 286.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 180 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Human Fibroblast

DOSE/DURATION :: 50 mg/L

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 33,3823,1984

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S24/25

[ WGK Germany ]:
3

[ RTECS ]:
LK9250000

[ HS Code ]:
2914501900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2914501900

[ Summary ]:
2914501900 other ketone-phenols。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%